Two intermediates in the synthesis of decahydroisoquinolines with NMDA and AMPA receptor antagonist activity

Acta Crystallogr C. 2001 Sep;57(Pt 9):1089-91. doi: 10.1107/s0108270101009702. Epub 2001 Sep 11.

Abstract

In 6-methyl-N-(4-nitrobenzoyl)-5,6-dihydropyridin-2(1H)-one, C(13)H(12)N(2)O(4), (I), the piperidone ring is in a distorted half-chair conformation. In 8-methoxy-3-methyl-N-(4-nitrobenzoyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline-1,6-dione, C(18)H(20)N(2)O(6), (II), the heterocyclic ring is in a slightly distorted half-boat conformation, while the other six-membered ring is in a distorted chair conformation. Compound (II) presents a strong intramolecular C-H...O hydrogen bond. In both (I) and (II), the molecules interact through C-H...O interactions.

MeSH terms

  • Crystallography, X-Ray
  • Excitatory Amino Acid Antagonists / chemical synthesis
  • Excitatory Amino Acid Antagonists / chemistry*
  • Isoquinolines / chemical synthesis
  • Isoquinolines / chemistry*
  • Molecular Structure
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Receptors, AMPA / antagonists & inhibitors*
  • Receptors, N-Methyl-D-Aspartate / antagonists & inhibitors*

Substances

  • 6-methyl-N-(4-nitrobenzoyl)-5,6-dihydropyridin-2(1H)-one
  • 8-methoxy-3-methyl-N-(4-nitrobenzoyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline-1,6-dione
  • Excitatory Amino Acid Antagonists
  • Isoquinolines
  • Nitro Compounds
  • Pyridines
  • Quinolines
  • Receptors, AMPA
  • Receptors, N-Methyl-D-Aspartate